JPS60185706A - Aminoalkane phosphoric acid and derivatives as fungicide - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to methods of killing fungi or inhibiting fungal growth using branched aminoalkane phosphonic acids and phosphonic acid derivatives. These compounds are effectively used as fungicides for several purposes and are particularly suitable for controlling fungal diseases of plants. The invention also relates to compositions containing certain of these compounds.

The use of certain linear aminoalkane phosphonic acids as fungicides is already known. U.S. Patent No. 3.76≠
, Otsu No. 77 describes the use of certain esters of certain linear aminoalkane phosphonic acids, namely diethyl β-aminoethyl phosphonate, as having bactericidal properties. Other diesters of straight-chain aminoalkanephosphonic acids, allyl esters and propynyl esters of aminomethylphosphonic acids are also disclosed in Soviet Patent No. 337j 7
? It is known to have bactericidal activity as described in No.

According to the invention, branched aminoalkanephosphonic acids and aminoalkanephosphonic acid derivatives.

It has been shown that it is a valuable fungicide that can be used to protect a variety of objects from fungal attack, and is particularly useful as a fungicide against fungi that cause disease in plants. Branched aminoalkanephosphonic acids and aminoalkanephosphonic acid derivatives are useful in agriculture and horticulture as fungicides against fungi that cause diseases in plants.
for example.

Used in seed dressings, leaf sprays, etc. Here, branched aminoalkanephosphonic acids and aminoalkanephosphonic acid derivatives refer to aminoalkanephosphonic acids and yohyaminoalkanephosphonic acid derivatives containing at least one substituent in the alpha position with respect to the phosphonic group.

The branched aminoalkanephosphonic acids and their acid derivatives used according to the invention have the general formula:
represents an alkyl group having from g to g carbon atoms, and n is 0. /, is an integer of 2 or 3, R3 represents an alkyl group having / to 72 carbon atoms, and R4 is
hydrogen and/or an alkyl group having 72 carbon atoms), including their salts and esters.

It is understood that the active compounds of the formula given above can also exist in the form of their acid addition salts, which shall be acceptable in the intended field of use.

Branched aminoalkane phosphonic acids, for example.

Tetrahedron Letters No. 3.2 (
/77), pp. 2g23-2♂3≠, by condensing alkyl carbamates with aldehydes and triphenylphosphites. The salts here referred to as metal salts, ammonium salts, amine salts, salts of quaternary ammonium compounds and acid addition salts are prepared by methods known per se, for example as shown in the examples. Esters of phosphonic acids are e.g.
It can be produced by condensing acyl phosphate with trahydroxylamine and further reducing it. half ester.

It can be prepared from sidiesters by the use of ammonia.

Salts or free acids of aminoalkanephosphonic acids are particularly preferred. It is preferred that R4 and R2 are lower alkyl groups having /≠ carbon atoms, most preferably hydrogen.

As mentioned above, n is an integer from O to 3, suitably from O to λ. An important feature of the compounds used according to the invention is the α-substitution on the phosphonic group by one or λ alkyl groups.

The number of carbon atoms in these alkyl groups R5 and R4 should suitably not exceed ♂ and preferably should not exceed ♂.

When two branches are present, the total number of carbon atoms should suitably not exceed r and preferably should not exceed j. 75,000, preferred compounds contain short branches. Particular preference is given to using compounds with only 7 alpha substitutions.

As mentioned above, the active compound may be in the form of its acid addition salts which are acceptable for the intended use. Although salts of organic acids can be used here, acid addition salts are preferably salts with mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid.

As metal salts, first of all the alkali metal, alkaline earth metal, copper, cobalt, zinc, tin and aluminum salts come into consideration. Salts of amines include: salts of aromatic or cycloaliphatic or aliphatic primary, secondary, or tertiary amines containing higher or lower aliphatic groups, such as aniline and alphanaphthylamine. and salts of cyclic amines such as morpholine and pyrrolidine and related compounds and salts of polyamine compounds having seven or more amine groups participating in salt formation with phosphonic acids. Quaternary ammonium salts of aminophosphonic acids include: salts of short chain length quaternary ammonium compounds having / to 5 carbon atoms, such as the salts of tetramethylammonium compounds and tetrabutylammonium compounds; Quaternary ammonium compounds containing 7 or more hydrophobic groups, such as alkyltrimethylammonium compounds, dimethyldialkyl ammonium compounds, benzyldimethylalkylammonium compounds (wherein the alkyl chain contains from 1 to 20 carbon atoms) and 7
Salts of corresponding quaternary ammonium compounds containing more than 3 alkylene groups.

Esters of acids refer to diesters and monoesters, ie half esters, suitably those having / to ≠ lower alkyl groups.

The invention therefore provides for contacting a fungus, or a substance or host under the control of a fungus, or a substance or host susceptible to attack by a fungus, with a branched aminoalkane phosphonic acid or phosphonic acid compound as defined above. The present invention relates to a method for sterilizing or inhibiting the growth of fungi. The compound is used in an amount effective to kill or inhibit the fungus in question, with the dosage being as low as the desired level of protection.

It is determined based on the substance to be treated, the treatment method, etc.

Among the compounds used as fungicides according to the invention,
It has become clear that compounds in which n is η have very good bactericidal activity, and in particular, compounds having 7 ethyl groups, i.e., /-aminopropanephosphonic acid and its salts, have good bactericidal activity. Ta.

Branched aminoalkane phosphonic acids and phosphonic acid derivatives are useful for controlling fungi that cause diseases in plants, i.e.
It is primarily intended for use on farms. However, they are also useful in other fields as fungicides, e.g. in the field of protection of wood and wood-based products, animals and animal products, and as industrial fungicides they are useful, e.g. It can be used for the protection of fabrics, textiles, paper, leather, paints and other products and substances that are susceptible to fungi.

In the control of fungi that cause plant diseases, compounds can be used on seeds,
It can be used for the protection of fruits, bulbs, leaves and plants. The compounds and compositions containing an effective amount thereof are particularly useful in agriculture, particularly as seed dressings and foliar fungicides.

Compounds are soluble in water, and solubility is determined by structure and -
Depending on the situation, the compound may normally be used in the form of a water-based formulation. The compounds may also be used in formulations with conventional carriers and diluents. The compounds may also be included in solid formulations such as powders and pellets with carriers such as talc, clays, silicates, and the like. Liquid formulations include a diluent such as water and/or a solvent such as ethanol,
Contains ethyl acetate, glycerol, vegetable oil, dimethylformamide, N-methylpyrrolidone, etc. For the formulation of the active compounds according to the invention, customary additives and auxiliaries may be added to the powder, dust and liquid formulations. Examples of such include surfactants, wetting agents, stabilizers, and the like. The active compounds of the invention are compatible with other types of agents having fungicidal and biocidal activity, such as insecticides, and may be used in combination with these agents if desired. For the treatment of wood, the compounds may be used, for example, in mixtures with known wood preservatives, with quaternary ammonium compounds of the type having at least 7 hydrophobic groups, such as those mentioned above, and with other alkyl It can be used as a mixture with ammonium compounds. The concentration of active substance in such formulations for agricultural use is usually between 0 and 0% by weight.

The compound is derived from the fungus genus Drachslera, 5eptorla nodor.
um (Monotriano.

thorium), Ustllago hordai and other crop-causing fungi and can therefore be used advantageously as a seed dressing.

The compounds furthermore exhibit good efficacy as wood preservatives and therefore the use of the compounds for protecting timber, wood and wood-based products from fungal attack is a preferred embodiment of the invention. becomes.

In addition to the uses of branched aminoalkane phosphonic acids and phosphonic acid derivatives as described above, the present invention provides certain compositions containing branched aminoalkane phosphonic acids and aminoalkane phosphonic acid compounds for use as fungicides. It also relates to things.

Accordingly, 1 the present invention provides a disinfectant containing as an active ingredient /-aminopro/4-phosphonic acid or an acid addition salt thereof, comprising a conventional inert carrier and diluent and optionally conventional additives. Regarding the composition.

The invention comprises conventional inert carriers and diluents, and optionally conventional additives, as active ingredients of the general formula: where R1 and R2 are independent of each other and represent hydrogen. represents an alkyl group having or/to r carbon atoms, preferably represents hydrogen, and n is 0./, 2
or an integer of 3, preferably an integer of 0 to λ, R
3 represents /A to an alkyl group having 72 carbon atoms, R4tl represents hydrogen, or /A represents an alkyl group having 72 carbon atoms, preferably hydrogen) The present invention relates to a disinfectant composition characterized in that it contains a salt or ester or an acid addition salt thereof.

Salts of these acids in the composition are metal salts, ammonium salts, amine salts and salts of quaternary ammonium compounds.

Esters and half-esters suitably contain alkyl groups having / to t carbon atoms.

Preference is given to said compositions in which the active substance is a salt.

Metal salts include, for example, alkali metal, alkaline earth metal, copper, cobalt, zinc, tin and aluminum salts. Salts of amines include: salts of aromatic or cycloaliphatic or aliphatic primary, secondary, or tertiary amines containing higher or lower aliphatic groups, and cyclic amines. For example, morpholine and pyrrolidine salts and related compounds. Amines include mono-, di- and polyamines. Quaternary ammonium compounds capable of forming salts with branched aminoalkane phosphonic acids include ammonium compounds of short chain length, such as tetrabutylammonium compounds, and quaternary compounds having 7 or more hydrophobic groups (other groups may be short, e.g. (alkyl group or hydroxyalkyl group). These quaternary ammonium compounds include, for example, alkyltrimethylammonium compounds, dimethyldialkyl ammonium compounds, benzyldimethylalkylammonium compounds (wherein the alkyl chain contains from 1 to 20 carbon atoms) and the corresponding alkylene groups. It may be a quaternary ammonium compound containing.

The invention is further illustrated by the following example. Unless otherwise specified, parts and numbers refer to parts by weight.

Example / /-7 Preparation of minonoropanephosphonic acid Ethyl carbamate (lA4), triphenyl phosphite (/yoyo I) and fopa f-# (IAot
g) was heated with acetic acid [10 ml] under reflux for 1 hour. Concentrated hydrochloric acid (sotrtt) was added and the mixture was heated under reflux for two hours before being cooled.

The aqueous phase was separated and washed with benzene ('20 ml), then
Evaporated to dryness. The residue was dissolved in methanol (4 tomt) and propylene oxide was added until the mixture became clear. This crude phosphonic acid was separated and recrystallized from water/methanol to yield a fine white crystalline solid (2 g of lA, 0.≠%) with a melting point of 26≠~2°C.

Example 2 /-aminopropanephosphonic acid c3.9ji.

, 214t mmol) and /, O-diaminohexane (ftj1/, /'A2 mmol)'i
t, dissolved in water, and the water was distilled off. Ethanol (CjOTll) was then added and the ethanol was then distilled off. The residue was dried in a vacuum oven at 50°C for μ hours and the above salt had a melting point of 21/lIA to 230°C.
It was obtained as a fine crystalline solid with (!, ri, λ%).

Example 3 /-aminopropanephosphonic acid (,2,ri/I.

20, mmol) and tetrabutylammonium bromide (1,741/, 20, mmol),
Water (jθml), propylene oxide C20ml) and water (θml) were added. Next, the obtained solution was
Heated to 0°C for //2 hours and then cooled. After evaporating the volatile components, first in a vacuum furnace! Dry at Q℃ for 2 hours,
Further, when dried with silica gel for j days, the desired compound was obtained as a colorless viscous oil C7JIl.

P44.2%).

Rehiro /-7 Minopropanephosphonic acid (v, zsip.

371 mmol) Oh! CF copper acetate hydrate (7:
g/, 2 g, 37. /? mmol) in water and then the water was distilled off.

Water C in the residue! Add water, filter the solids, wash with acetone (2x, 20ml), then boil in a vacuum oven.
After drying at 0 for 3 hours, the desired copper salt was obtained as a blue-green powder (1.PO, 2%).

example! Production of morpholine salt q of l-aminozolonophosphonic acid/-aminopropanephosphonic acid (lAO/, 9°J (
S': (S' mmol) and morpholine (1021
,! After dissolving 7.7 mmol) in water (20 ml), ethanol (201 rLl) was added. After evaporating the solvent and excess amine, acetone (jO
m/), filter the solids and add acetone (soynt
) and then dried in a vacuum oven at 60°C for μ hours to obtain the morpholine salt of /-aminopronophosphonic acid C! with a melting point of 1.2 to ≠°C. , j11. 1A11t%)
was gotten. Similarly, the following amine #i was obtained: yield and melting point are given in parentheses.

3-Hydroprobylamine (71.1%, 756-76
0℃).

Dichlorohexylamine (Riotsu, 3%, 21.0-21
, 1/-℃).

Pyrrolidine (Rice, J%, 76-7°C).

Diethylamine (5%, rμ and 1°C).

741-1.91-10 I°C.

Hexylamine (3% RIA, 2AA~2g°C).

N,N-dimethylethanolamine (%1.2~264°C).

All salts prepared according to the examples above are 13C
This was confirmed by characterization by O and 'H nuclear magnetic resonance spectroscopy.

Example B The following compounds were tested for bactericidal activity: (0H)2P-C-NH2 3 3R4 /) CH, H 2) 02H5H 3) CHCCH3) 2H C, Hl, H j) OH, CH3 O) C2H5C2H5 7 ) CH(CH3)2CH3 f) C3H,H ri) 04H2H l's 05H41H //) C2H3H (as potassium salt)/, 2) C
2H3H (f14(Ji) salt) The activity of each substance is
The following method was used to investigate mycelium growth inhibition test on agar.

The material was dissolved in sterile potato dextrose agar (PDA) to a concentration of 600 ppm. The mixture was poured into a standard bedding dish with a diameter chisel. Agar plugs (jIn
lll diameter) was placed in the center of each Petri dish. Depending on the growth speed of each picture! After incubation at 2g° C. for 1 to 3 weeks, the diameter of growth was measured and compared to the diameter of growth on untreated dishes.

The effect is that for some compounds, Dreehslea
5ativa, whereas for certain compounds Drec
tested against halea tere@.

The table shows the results by classifying the compounds according to the following scale: 0 = Growth from 0 to . 25% inhibition control - 26-50% inhibition of growth No 3/-75% inhibition of growth 3 = 76-100 inhibition of growth Below margin compound p, 5ativa control 3 3 3 ≠ 3 3 2 3 D-teres+ Control 3 Ta 3 10 2 °゛1/3 /, 2 2 Dosage as in the previous case! 00 ppm of some compounds, Fusarim cul
tested against morum. The compounds tested were numbered 3.3 and λ, respectively.
control.

Similarly, several salts of compound 2 were prepared at a dosage of 300
Tested at ppm against Rh1zoetonia 5olani. The salts were a) 7ethylamine salt, b) cyclohexylamine salt, C) morpholine salt, d) pyrrolidine salt (all of which were control 3).

Example 7 The effect of several compounds according to the invention on Drechslera teres was investigated by in vivo tests.

The test was conducted according to the oamos-method. This method involves dressing seeds on filter paper moistened with a buffered sugar solution.
eed). Next, place the F paper into a transparent glass plate with a lid. The temperature was maintained at 22° C. and the dishes were placed in a cabinet controlled by a thermostand with alternating cycles of 2 hours of light and 72 hours of darkness.

The survey was conducted one week later. Seeds that survive show grown mycelia that form stains, but do not germinate due to osmotic pressure. Seeds with live bacteria are identified by color test. The method is rather rigorous, counting all seeds with live fungi (even seeds with a small amount of infection not seen on the growing plant). The results of the tests are expressed as percent control and the infection of untreated seeds in each test is taken as iqo%.

The following salts of l-aminopropanephosphonic acid were added to seeds,
Tested at a dosage of 2 kg/2-aqueous solution <; oqb active ingredient): a) Cyclohexylamine salt.

b) Hydroxypropylamine salt.

The results are shown below: a) Otsu≠ b), ? c) 74t dL5;+2 @'>417 Example In this example, the effect of /-aminopropanephosphonic acid as a foliar fungicide was investigated.

Agnet& seed barley (6 rows) was grown in standard soil for 2 days to stage/, 2 (IO base code for growth stage). The growth environment was 10,000 lux, g hours of illumination, and a temperature of 1/2 to 20°C.

Powdery mildew spores from infected plants, Prys i ph
egraminis f, sp, hordei (Erysphi graminis f.

Sp., Holdi) was sprinkled on uninfected plants. Cultivation was carried out in a humid chamber at 17°C for 1≠h at lOOh humidity. The plants were then returned to the greenhouse.

Infection started after 5 days and results were recorded after K days.

The test was a prevention test in which the plants were sprayed with the active compound prior to infection. An aqueous solution containing jθθ ppm of aminophosphonic acid was sprayed onto lθ plants in each pot. This solution is
A wetting agent was included and 6 pots or 60 plants were used for the test. For comparison, a commercial product (Forbel 7
! r011 a, i, /ha) was used in the same manner, and comparisons were also made with untreated plants. After the incubation period, the number of powdery mildew warts on the plants was counted and the results were as follows: untreated/4' (= θ% effect), treated with the substance according to the invention. 3<7! % effective), those treated with commercial products 0 (=/ 00% effective).

For example, these practical tests tested the effects of /-aminopropanephosphonic acid on a variety of fungi.

/, 5eptoria nodorum (lesions on leaves and galls) Materials and methods: @ S, winter wheat naturally infected with nodorum Ho
lme species was used for the test.

Weigh the wheat seeds and dose 2 mt with the formulation containing the compound.
/seed/ was treated as 9c20% active ingredient). Seeds were treated using a seed processor. Seeds were planted in autumn in test plots in a randomized block design (1 plot/, 3 x 10 m, l
1-replicate).

When the plants had 2-3 leaves, they were dug 2 m per section and attack on the coleoptiles was evaluated.

2Ustilago hordei (covered smut of barley)
(mut)) Materials and Methods Two barley old rka varieties were infected with spores of the brown sugar fungus ≠117 seeds/kg. Barley seeds were weighed and treated with the formulation (2 active ingredients), 2'd/seed/kg.

Seeds were sown in the spring in trial plots in a random block design.

The number of diseased panicles was evaluated for plots Z≠~/O≠m2//.

3. Drechslera teres (Net Spot Disease) Materials and Methods: Barley seeds of the Tellus variety, which are naturally infected with the fungus, Drechslera teres, were used in this study.

Seeds were treated as described above and then sown in the spring.

At the second leaf stage, plants with main attack on the second leaf were evaluated.

The attack is given as a numerical value related to the attack on untreated seeds (C=100%). The efficacy of the compound was determined by i4-cent control (
The results are shown in the table. The tests were conducted at two different locations and the results are presented separately.

Field trials investigated the effects of /-aminopropanephosphonic acid on a number of other fungi.

IATlletia caries (slug smut of autumn wheat) Materials and Methods: Autumn wheat Ho1me variety was infected with 39 to 9 spores/seed of the IATlletia fungus. After weighing the wheat seeds, the seeds were treated with the composition (2 active ingredients) and 2fnt. Seeds were treated using a seed treatment device. Seeds were planted in the autumn in a randomized block design test site (2 m'
The seeds were sown in the X/gm//compartment, Hiroko Replication).

The number of diseased panicles was counted in / Om2 / / plot.

, i Drechslera graminea (Barley Leaf Stripe) Materials and Methods: Fungus ]), barley Agneta species which had undergone a full natural infection with graminea (Graminia) were used in this study. Seeds were treated as described above with a composition of Seed/Yuto 9.2- and sown in the spring.

j-6 leaf stage (Feekes-Lage ig, IO
/m of the diseased plant with the hexadecimal code &31-32)
I counted the number of 2 toshi.

Drechslera avenave (oat net spot) Materials and Methods: Seeds of oat Se1ma naturally infected with the fungus, aver+ae, were used in this study.

Seeds were prepared at a dosage of 2 ml per J per kg of seeds (,20
% active ingredient (a, i,) ) processed.

At the 2-leaf stage, the number of diseased plants per m2 was counted.

ZU8tilago avenae (bare smut of oat oats) Materials and methods: Hedvig oat seeds were added to 31 ml of water.
was infected with a substance containing 3 g of spores of the brown sugar bacterium (wet infection under reduced pressure). Infected seeds were dried in a thin layer to a moisture content of approximately 15%. Dry infected seeds are
Seeds were treated with 2 ml/g of the composition (20 active ingredients) using a seed dressing machine.

Treated seeds were planted in the spring in a random block design test site (/, 3, j m x m / / plot, g replication).
It was sown in The number of diseased ears was counted and the result was 3m.
It was given as a number of 2.

The results of these field experiments are shown in the table below as described above.

Table (Treatment) 27 73 Test Site I (Treatment) ,! ,? 7Ir test site ■ (Treatment) 2. ! i>7.2 Test site I (Treatment) 0 100 Test site ■ (Treatment) 0.3 Taz7 (Treatment) / Dodo 2 Bacterial name Attack Control test site I (Treatment) 4L Ta O test site ■ (Treatment) ) l 99 Test Site I (Treatment) O10θ Test Site ■ (Treatment) 19' Test Site I (Treatment) Hirota Otsu Test Site ■ (Treatment) J Light As mentioned above, in the field test, Drechglera t
eres (Drechslera teres) and Drechs
lera avenae
The effect of a linear aminoalkanephosphonic acid, 3-aminozolopanephosphonic acid, with the same number of carbon atoms on t was investigated as a comparison. The control infections obtained with this compound were 2, 1 and 37, respectively.

Example 10 In this example, the effect of /-aminozolopanephosphonic acid on wood attacking fungi was tested.

The test was a pilot plant test at a sawmill;
PinusSilve with dimensions of 2 evenings x 100X≠000
STRIS plates were treated with a formulation consisting of l-aminozolopanephosphonic acid and a quaternary ammonium compound by immersing them in the solution. These plates were treated with Bacillus subtilis (mou
ld), blue fungi and rot ungi. The boards were stored vertically and crosswise and examined for bacterial attack after 6 days.

/-Aminozolopanephosphonic acid was used in combination with benzalkonium chloride (g% phosphonic acid and g0thipenzalkonium chloride, approximately 2 molar excess of the quaternary ammonium compound). 'The products of the invention are defined in the following table as a
). As a comparison, the same quaternary ammonium compound and gnylated (gua
A commercial product based on the nidated) compound was used. This product was then designated as b).

Aggression was assessed by visual inspection according to the following scale: 0 - no aggression.

l - Tends to attack (less than /chi on the surface).

! = Slight attack (/~3chi on the surface).

3-Attack (5-SO% of surface).

≠ = Severe attack (beyond the surface jochi).

The results are shown in the table below.

Margin below Product concentration (chi) Attack Attack Store vertically, store crosswise a) /, g /, 6 0.7 ! L) 2.7 /, / /, 7 a) 4’, 3 0.9 0.6 b) 3. / 3.0. 2.7 b) 3.1 /,! ;2.1 b) g, s, 2. 2.7 Unprocessed 3.3 3. Child side 11 11 Aminozorono and phosphonic acid salt paste.

The effect on Graminae was tested.

The salt-treated seeds were sown in several dishes containing moist soil mixed with gravel. The dishes were kept in a cool place at +6°C for 10 to 12 days and then brought to room temperature and irradiated until 2-3 leaves were reached. The number of developed plants and plants with characteristic slits on coleoptiles, leaves, roots, etc. were counted. The percentage of attack for each treatment is compared with that for untreated seeds (as lθO) and the seed tracing effect is shown below in this regard.

A) 3-hydroxyprobylamine salt (lOOti) B
) Piperazine salt (bis salt of piperazine) (Rlr%
) C) Hexamethylene diamine salt (bis acid salt) (/θ
θ Ch) D) Hexylamine salt (R♂%) E) Dimethylethanolamine salt (ioos) Example 12 /-The following salt of aminopropanephosphonic acid.

For Teres (D, Teresu), as described in Example B! ;00 ppm dose was tested.

A) Improvylamine salt B) Secondary butylamine salt C) Tetrabutylammonium salt Example Evaluation and classification according to the scale of B gave the following results.

A) 3 B) 3 C) 2 Example 13 The following substances were administered as described in Example 6Vc at a dosage of joθppm.
tested against F. Culmorum.

A) /-aminopropane phosphonic acid B) Diethyl/-aminopropane phosphonate C)
Diethyl aminoethane phosphonate (comparison) The results were as follows.

A) 2 B), 2 C) / Agent's name: Kawahara 1) - Ho Continuation of page 1 @Inventor Ax Bianca Igi Mu,

Claims (1)

[Claims] (1) In a method of sterilizing or inhibiting the growth of fungi, fungi, or substances or hosts under the control of fungi, or substances or hosts susceptible to attack by fungi, are defined by the general formula: , R1 and R2 are unrelated to each other and represent hydrogen or/and an alkyl group having g carbon atoms, and n is an integer of 0./, 2 or 3;
R3 represents an alkyl group having / to 72 carbon atoms, R4 represents hydrogen or / to 7.2
or a salt, ester or acid addition salt thereof. (2) R3 is/is! 2. A process according to claim 1, wherein R4 is hydrogen and/or an alkyl group having 5 carbon atoms. (3) The method according to claim 1 or 2, wherein R4 is hydrogen. (4) The method according to claim 1, wherein R, C and R2 are all hydrogen. (5) The method according to claim 1, wherein the salt is an ammonium salt, an amine salt, or a salt of a quaternary ammonium compound. (6) The method according to claim 1, wherein the salt is a metal salt. (7) The method according to claim 1, wherein the compound is /-aminopropanephosphonic acid, a salt or ester thereof, or an acid addition salt thereof. (8) A germicidal composition comprising an inert carrier and a diluent, characterized in that it contains an aminoalkanephosphonic acid, a salt or ester thereof, or an acid addition salt thereof as an active ingredient. (9) Inert carrier and a diluent, the active ingredient having the general formula: (wherein R1 and R2 are unrelated to each other and represent hydrogen or /
represents an alkyl group having from g to g carbon atoms, and n is 0. /, is an integer of 2 or 3, R3 represents an alkyl group having / to 72 carbon atoms, R4 is
A disinfectant composition characterized in that it contains a salt or ester of a compound (representing hydrogen and/or an alkyl group having from 72 carbon atoms) or an acid addition salt thereof. (11) The disinfectant composition according to claim 1, wherein the salt is a metal salt, an ammonium salt, an amine salt, or a salt of a quaternary ammonium compound.